NPASS Compound

Structure

CID277784 OpenBabel06191716082D 38 42 0 0 1 0 0 0 0 0999 V2000 -6.2788 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7147 -3.7112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0823 -0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0768 -0.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7044 -3.2564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9898 -2.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9013 -1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4546 -4.5436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0388 -2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4965 -4.2346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1977 -3.8745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4836 -1.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8958 -1.9886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2396 -4.9037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1488 -4.1835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 2.2294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 0.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4781 -1.2841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -1.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3025 -2.9022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 37 1 0 0 0 0 2 38 1 0 0 0 0 3 5 2 0 0 0 0 3 15 1 0 0 0 0 4 6 2 0 0 0 0 4 16 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 15 1 0 0 0 0 7 21 2 0 0 0 0 8 15 2 0 0 0 0 8 26 1 0 0 0 0 9 17 2 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 10 19 2 0 0 0 0 11 16 2 0 0 0 0 11 27 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 13 22 1 0 0 0 0 14 20 1 0 0 0 0 14 25 2 0 0 0 0 18 31 1 0 0 0 0 19 32 1 0 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 21 28 1 0 0 0 0 22 30 2 0 0 0 0 23 26 2 0 0 0 0 23 34 1 0 0 0 0 24 27 2 0 0 0 0 24 35 1 0 0 0 0 25 30 1 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 27 38 1 0 0 0 0 28 17 1 1 0 0 0 28 29 1 0 0 0 0 29 16 1 6 0 0 0 29 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.16
Volume:	520.702
LogP:	4.167
LogD:	3.288
LogS:	-3.461
# Rotatable Bonds:	5
TPSA:	139.84
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	3.717
Fsp3:	0.133
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.804
MDCK Permeability:	7.936998372315429e-06
Pgp-inhibitor:	0.522
Pgp-substrate:	0.08
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	93.68814086914062%
Volume Distribution (VD):	0.64
Pgp-substrate:	4.044605255126953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.838
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.405
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.673
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.105
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.59
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	13.011
Half-life (T1/2):	0.767

ADMET: Toxicity

hERG Blockers:	0.224
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.42
AMES Toxicity:	0.224
Rat Oral Acute Toxicity:	0.472
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.962
Carcinogencity:	0.043
Eye Corrosion:	0.003
Eye Irritation:	0.888
Respiratory Toxicity:	0.727

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC277784

Natural Product ID:	NPC277784
*Common Name:**	Gnetulin
IUPAC Name:	(1E,2S,3S)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-[(4-hydroxy-3-methoxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol
Synonyms:	Gnetulin
Standard InCHIKey:	YUGHGAXRXHODHK-MGOPEXEZSA-N
Standard InCHI:	InChI=1S/C30H26O8/c1-37-26-8-15(3-5-23(26)34)7-21-22-13-20(33)14-25(36)30(22)29(16-4-6-24(35)27(11-16)38-2)28(21)17-9-18(31)12-19(32)10-17/h3-14,28-29,31-36H,1-2H3/b21-7-/t28-,29+/m0/s1
SMILES:	COc1cc(ccc1O)/C=C1/c2cc(O)cc(c2[C@@H]([C@H]1c1cc(O)cc(c1)O)c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1818263
PubChem CID:	56673069
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO39	Actaea asiatica	Species	Ranunculaceae	Eukaryota	roots, rhizomes	n.a.	n.a.	PMID[17067171]
NPO1888	0dularia harveyana	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4697	Gnetum ula	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3783	Geodia lindgreni	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO39	Actaea asiatica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5631	Taraktogenos heterophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2820	Artocarpus venenosa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6593	Mollisia ventosa	Species	Dermateaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	70160.0	nM	PMID[475238]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC277784 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	487
0.1-0.2	1811
0.2-0.3	4722
0.3-0.4	12923
0.4-0.5	5235
0.5-0.6	4450
0.6-0.7	8164
0.7-0.8	3895
0.8-0.85	658
0.85-0.9	311
0.9-0.95	37
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9416	High Similarity	NPC472091
0.9416	High Similarity	NPC472090
0.9416	High Similarity	NPC472092
0.9281	High Similarity	NPC472087
0.9281	High Similarity	NPC472088
0.9209	High Similarity	NPC472089
0.9143	High Similarity	NPC183709
0.9124	High Similarity	NPC313081
0.9065	High Similarity	NPC55947
0.9037	High Similarity	NPC126836
0.9014	High Similarity	NPC15659
0.9014	High Similarity	NPC304894
0.8986	High Similarity	NPC69029
0.8986	High Similarity	NPC10314
0.8986	High Similarity	NPC294884
0.8986	High Similarity	NPC200557
0.8986	High Similarity	NPC158142
0.8986	High Similarity	NPC108198
0.8966	High Similarity	NPC476969
0.8963	High Similarity	NPC471518
0.8963	High Similarity	NPC471519
0.8958	High Similarity	NPC262297
0.8944	High Similarity	NPC173203
0.8944	High Similarity	NPC163508
0.8929	High Similarity	NPC230124
0.8929	High Similarity	NPC6300
0.8929	High Similarity	NPC275061
0.8929	High Similarity	NPC184613
0.8929	High Similarity	NPC132804
0.8929	High Similarity	NPC220344
0.8929	High Similarity	NPC114171
0.8929	High Similarity	NPC243996
0.8921	High Similarity	NPC143139
0.8921	High Similarity	NPC202846
0.8913	High Similarity	NPC66840
0.8913	High Similarity	NPC209199
0.8913	High Similarity	NPC256307
0.8913	High Similarity	NPC125649
0.8905	High Similarity	NPC161958
0.8905	High Similarity	NPC14224
0.8897	High Similarity	NPC329836
0.8889	High Similarity	NPC211758
0.8889	High Similarity	NPC126291
0.8889	High Similarity	NPC87794
0.8865	High Similarity	NPC12668
0.8865	High Similarity	NPC22317
0.8865	High Similarity	NPC308768
0.8857	High Similarity	NPC242715
0.8857	High Similarity	NPC22902
0.8857	High Similarity	NPC56329
0.8857	High Similarity	NPC230919
0.8857	High Similarity	NPC200935
0.8857	High Similarity	NPC266453
0.8857	High Similarity	NPC94994
0.8849	High Similarity	NPC241241
0.8841	High Similarity	NPC32778
0.8832	High Similarity	NPC238168
0.8832	High Similarity	NPC473309
0.8832	High Similarity	NPC232275
0.8832	High Similarity	NPC237424
0.8815	High Similarity	NPC236791
0.8815	High Similarity	NPC127587
0.8815	High Similarity	NPC324112
0.8815	High Similarity	NPC82679
0.8815	High Similarity	NPC246620
0.8815	High Similarity	NPC74817
0.8815	High Similarity	NPC124452
0.8815	High Similarity	NPC293054
0.8815	High Similarity	NPC159968
0.8815	High Similarity	NPC282000
0.8815	High Similarity	NPC169474
0.8811	High Similarity	NPC469630
0.8794	High Similarity	NPC105847
0.8794	High Similarity	NPC243759
0.8794	High Similarity	NPC29868
0.8794	High Similarity	NPC79622
0.8794	High Similarity	NPC212942
0.8794	High Similarity	NPC218131
0.8786	High Similarity	NPC300846
0.8786	High Similarity	NPC114155
0.8786	High Similarity	NPC30632
0.8786	High Similarity	NPC476639
0.8777	High Similarity	NPC56764
0.8777	High Similarity	NPC289258
0.8777	High Similarity	NPC276026
0.8777	High Similarity	NPC469659
0.8777	High Similarity	NPC555
0.8777	High Similarity	NPC7515
0.8777	High Similarity	NPC160697
0.8777	High Similarity	NPC206737
0.8777	High Similarity	NPC188378
0.8768	High Similarity	NPC6451
0.8768	High Similarity	NPC474134
0.8768	High Similarity	NPC131128
0.8759	High Similarity	NPC254000
0.875	High Similarity	NPC317237
0.875	High Similarity	NPC44530
0.875	High Similarity	NPC154866
0.875	High Similarity	NPC277951
0.8741	High Similarity	NPC76451
0.8741	High Similarity	NPC28730
0.8741	High Similarity	NPC470917
0.8741	High Similarity	NPC175838
0.8741	High Similarity	NPC191231
0.8741	High Similarity	NPC18924
0.8741	High Similarity	NPC78974
0.8741	High Similarity	NPC44748
0.8741	High Similarity	NPC214406
0.8741	High Similarity	NPC223136
0.8741	High Similarity	NPC103823
0.8723	High Similarity	NPC151656
0.8723	High Similarity	NPC6262
0.8723	High Similarity	NPC201145
0.8723	High Similarity	NPC272157
0.8723	High Similarity	NPC266006
0.8723	High Similarity	NPC90615
0.8723	High Similarity	NPC73535
0.8723	High Similarity	NPC25111
0.8716	High Similarity	NPC321972
0.8716	High Similarity	NPC324517
0.8716	High Similarity	NPC329343
0.8714	High Similarity	NPC180602
0.8714	High Similarity	NPC214853
0.8714	High Similarity	NPC240279
0.8714	High Similarity	NPC55239
0.8707	High Similarity	NPC318373
0.8707	High Similarity	NPC321657
0.8707	High Similarity	NPC211561
0.8696	High Similarity	NPC45715
0.8696	High Similarity	NPC474356
0.8696	High Similarity	NPC15543
0.8696	High Similarity	NPC12275
0.8686	High Similarity	NPC212015
0.8681	High Similarity	NPC155392
0.8681	High Similarity	NPC274721
0.8681	High Similarity	NPC135767
0.8676	High Similarity	NPC252131
0.8676	High Similarity	NPC266555
0.8671	High Similarity	NPC178054
0.8667	High Similarity	NPC113495
0.8667	High Similarity	NPC299584
0.8667	High Similarity	NPC105925
0.8667	High Similarity	NPC472093
0.8667	High Similarity	NPC234400
0.8667	High Similarity	NPC17943
0.8667	High Similarity	NPC265483
0.8667	High Similarity	NPC251855
0.8667	High Similarity	NPC60885
0.8667	High Similarity	NPC82483
0.8667	High Similarity	NPC116907
0.8667	High Similarity	NPC233410
0.8667	High Similarity	NPC298757
0.8667	High Similarity	NPC221077
0.8667	High Similarity	NPC157333
0.8667	High Similarity	NPC57490
0.8667	High Similarity	NPC117214
0.8667	High Similarity	NPC208950
0.8667	High Similarity	NPC203133
0.8667	High Similarity	NPC193544
0.8667	High Similarity	NPC475169
0.8657	High Similarity	NPC197757
0.8657	High Similarity	NPC228922
0.8657	High Similarity	NPC121115
0.8652	High Similarity	NPC265433
0.8652	High Similarity	NPC205442
0.8652	High Similarity	NPC248727
0.8652	High Similarity	NPC162659
0.8652	High Similarity	NPC270456
0.8652	High Similarity	NPC133025
0.8649	High Similarity	NPC477612
0.8643	High Similarity	NPC317380
0.8643	High Similarity	NPC141023
0.8639	High Similarity	NPC227516
0.8639	High Similarity	NPC20757
0.8633	High Similarity	NPC303144
0.863	High Similarity	NPC317053
0.863	High Similarity	NPC260397
0.863	High Similarity	NPC324492
0.8623	High Similarity	NPC299221
0.8623	High Similarity	NPC192687
0.8623	High Similarity	NPC311680
0.8623	High Similarity	NPC224157
0.8623	High Similarity	NPC234488
0.8623	High Similarity	NPC51840
0.8621	High Similarity	NPC28440
0.8621	High Similarity	NPC171932
0.8621	High Similarity	NPC473108
0.8613	High Similarity	NPC28765
0.8609	High Similarity	NPC202104
0.8603	High Similarity	NPC223953
0.8601	High Similarity	NPC34431
0.8601	High Similarity	NPC262189
0.8601	High Similarity	NPC184797
0.8601	High Similarity	NPC73505
0.8601	High Similarity	NPC295719
0.8601	High Similarity	NPC266197
0.8601	High Similarity	NPC309124
0.8601	High Similarity	NPC291101
0.8601	High Similarity	NPC165026
0.8592	High Similarity	NPC301765

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC277784 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	417
0.1-0.2	966
0.2-0.3	1710
0.3-0.4	2866
0.4-0.5	1615
0.5-0.6	965
0.6-0.7	524
0.7-0.8	81
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8417	Intermediate Similarity	NPD3027	Phase 3
0.8214	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD4908	Phase 1
0.8143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD3620	Phase 2
0.8112	Intermediate Similarity	NPD1613	Approved
0.8112	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7199	Phase 2
0.8099	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD3018	Phase 2
0.7862	Intermediate Similarity	NPD6234	Discontinued
0.7836	Intermediate Similarity	NPD5283	Phase 1
0.7771	Intermediate Similarity	NPD37	Approved
0.773	Intermediate Similarity	NPD2982	Phase 2
0.773	Intermediate Similarity	NPD2983	Phase 2
0.7714	Intermediate Similarity	NPD1610	Phase 2
0.7687	Intermediate Similarity	NPD228	Approved
0.766	Intermediate Similarity	NPD2981	Phase 2
0.7655	Intermediate Similarity	NPD4625	Phase 3
0.7639	Intermediate Similarity	NPD2861	Phase 2
0.7636	Intermediate Similarity	NPD7228	Approved
0.7625	Intermediate Similarity	NPD4966	Approved
0.7625	Intermediate Similarity	NPD4967	Phase 2
0.7625	Intermediate Similarity	NPD4965	Approved
0.7607	Intermediate Similarity	NPD6232	Discontinued
0.7606	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7473	Discontinued
0.7537	Intermediate Similarity	NPD3021	Approved
0.7537	Intermediate Similarity	NPD3022	Approved
0.7529	Intermediate Similarity	NPD8054	Approved
0.7529	Intermediate Similarity	NPD8053	Approved
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6166	Phase 2
0.7515	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4060	Phase 1
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4749	Approved
0.7448	Intermediate Similarity	NPD4624	Approved
0.7438	Intermediate Similarity	NPD1934	Approved
0.7429	Intermediate Similarity	NPD1548	Phase 1
0.7403	Intermediate Similarity	NPD3892	Phase 2
0.7391	Intermediate Similarity	NPD2801	Approved
0.7338	Intermediate Similarity	NPD6674	Discontinued
0.7333	Intermediate Similarity	NPD3657	Discovery
0.7333	Intermediate Similarity	NPD5735	Approved
0.7329	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5763	Approved
0.732	Intermediate Similarity	NPD5762	Approved
0.732	Intermediate Similarity	NPD3540	Phase 1
0.7301	Intermediate Similarity	NPD3882	Suspended
0.7285	Intermediate Similarity	NPD4097	Suspended
0.7284	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1465	Phase 2
0.7278	Intermediate Similarity	NPD5844	Phase 1
0.726	Intermediate Similarity	NPD3094	Phase 2
0.7256	Intermediate Similarity	NPD7831	Phase 2
0.7256	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7833	Phase 2
0.7255	Intermediate Similarity	NPD3539	Phase 1
0.725	Intermediate Similarity	NPD4005	Discontinued
0.7248	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8127	Discontinued
0.7222	Intermediate Similarity	NPD3092	Approved
0.7222	Intermediate Similarity	NPD3705	Approved
0.7193	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1653	Approved
0.7153	Intermediate Similarity	NPD4750	Phase 3
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1511	Approved
0.7152	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7041	Phase 2
0.7152	Intermediate Similarity	NPD4055	Discovery
0.7151	Intermediate Similarity	NPD7240	Approved
0.7135	Intermediate Similarity	NPD7074	Phase 3
0.7133	Intermediate Similarity	NPD5109	Approved
0.7133	Intermediate Similarity	NPD5111	Phase 2
0.7133	Intermediate Similarity	NPD5110	Phase 2
0.7126	Intermediate Similarity	NPD6959	Discontinued
0.7123	Intermediate Similarity	NPD5327	Phase 3
0.7118	Intermediate Similarity	NPD8252	Approved
0.7118	Intermediate Similarity	NPD3818	Discontinued
0.7118	Intermediate Similarity	NPD8251	Approved
0.7118	Intermediate Similarity	NPD8099	Discontinued
0.7115	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7447	Phase 1
0.7097	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7124	Phase 2
0.7086	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7054	Approved
0.7076	Intermediate Similarity	NPD8156	Discontinued
0.707	Intermediate Similarity	NPD3750	Approved
0.7063	Intermediate Similarity	NPD3091	Approved
0.7063	Intermediate Similarity	NPD1512	Approved
0.7059	Intermediate Similarity	NPD6353	Approved
0.7051	Intermediate Similarity	NPD7037	Approved
0.7048	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4357	Discontinued
0.7044	Intermediate Similarity	NPD7213	Phase 3
0.7044	Intermediate Similarity	NPD7212	Phase 2
0.7039	Intermediate Similarity	NPD4140	Approved
0.7039	Intermediate Similarity	NPD1558	Phase 1
0.7035	Intermediate Similarity	NPD7472	Approved
0.7032	Intermediate Similarity	NPD6099	Approved
0.7032	Intermediate Similarity	NPD6100	Approved
0.703	Intermediate Similarity	NPD3817	Phase 2
0.703	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD940	Approved
0.7015	Intermediate Similarity	NPD846	Approved
0.7011	Intermediate Similarity	NPD7549	Discontinued
0.7006	Intermediate Similarity	NPD5177	Phase 3
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2489	Approved
0.7	Intermediate Similarity	NPD27	Approved
0.6994	Remote Similarity	NPD7028	Phase 2
0.6994	Remote Similarity	NPD4380	Phase 2
0.6993	Remote Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD5536	Phase 2
0.6988	Remote Similarity	NPD7768	Phase 2
0.6987	Remote Similarity	NPD7266	Discontinued
0.698	Remote Similarity	NPD6584	Phase 3
0.6972	Remote Similarity	NPD7157	Approved
0.6968	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4626	Approved
0.6966	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4059	Approved
0.6964	Remote Similarity	NPD5494	Approved
0.6962	Remote Similarity	NPD7466	Approved
0.6962	Remote Similarity	NPD6331	Phase 2
0.6957	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7095	Approved
0.6943	Remote Similarity	NPD970	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1242	Phase 1
0.6937	Remote Similarity	NPD7390	Discontinued
0.6933	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2238	Phase 2
0.6918	Remote Similarity	NPD5241	Discontinued
0.6918	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7906	Approved
0.6908	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6798	Discontinued
0.6906	Remote Similarity	NPD5451	Approved
0.6903	Remote Similarity	NPD6111	Discontinued
0.6899	Remote Similarity	NPD3060	Approved
0.6897	Remote Similarity	NPD1357	Approved
0.6897	Remote Similarity	NPD6797	Phase 2
0.6894	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6788	Approved
0.6882	Remote Similarity	NPD7229	Phase 3
0.6882	Remote Similarity	NPD7680	Approved
0.6882	Remote Similarity	NPD3051	Approved
0.6879	Remote Similarity	NPD7843	Approved
0.6875	Remote Similarity	NPD4577	Approved
0.6875	Remote Similarity	NPD4578	Approved
0.6871	Remote Similarity	NPD422	Phase 1
0.6867	Remote Similarity	NPD7819	Suspended
0.6866	Remote Similarity	NPD3020	Approved
0.6863	Remote Similarity	NPD2674	Phase 3
0.6859	Remote Similarity	NPD1510	Phase 2
0.6857	Remote Similarity	NPD7251	Discontinued
0.6857	Remote Similarity	NPD7685	Pre-registration
0.6855	Remote Similarity	NPD7003	Approved
0.6855	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4110	Phase 3
0.6855	Remote Similarity	NPD8166	Discontinued
0.6854	Remote Similarity	NPD4663	Approved
0.6853	Remote Similarity	NPD6671	Approved
0.6849	Remote Similarity	NPD5846	Approved
0.6849	Remote Similarity	NPD3019	Approved
0.6849	Remote Similarity	NPD6516	Phase 2
0.6849	Remote Similarity	NPD3095	Discontinued
0.6848	Remote Similarity	NPD5090	Approved
0.6848	Remote Similarity	NPD5089	Approved
0.6848	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD8651	Approved
0.6845	Remote Similarity	NPD3749	Approved
0.6842	Remote Similarity	NPD2970	Approved
0.6842	Remote Similarity	NPD2969	Approved
0.6839	Remote Similarity	NPD2157	Approved
0.6835	Remote Similarity	NPD2684	Approved
0.6824	Remote Similarity	NPD2230	Approved
0.6824	Remote Similarity	NPD2233	Approved
0.6824	Remote Similarity	NPD2232	Approved
0.6818	Remote Similarity	NPD943	Approved
0.6818	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1240	Approved
0.6818	Remote Similarity	NPD7808	Phase 3
0.6802	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2898	Approved
0.68	Remote Similarity	NPD4339	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data